74598-74-6Relevant academic research and scientific papers
Enones from Acid Fluorides and Vinyl Triflates by Reductive Nickel Catalysis
Pan, Feng-Feng,Guo, Peng,Li, Chun-Ling,Su, Peifeng,Shu, Xing-Zhong
supporting information, p. 3701 - 3705 (2019/05/24)
A nickel-catalyzed reductive coupling between acid fluorides and vinyl triflates has been described. This method provides an efficient access to various enones and avoids the requirement for acyl or vinyl metallic reagents in the conventional approaches.
Nickel-catalyzed carbonylative Negishi cross-coupling reactions
Wang, Qiaoling,Chen, Chuo
, p. 2916 - 2921 (2008/09/21)
Catalytic carbonylative Negishi cross-coupling reactions are described. This method readily provides various enones from enol triflates and diorganozinc reagents with catalytic amounts of nickel(II) chloride-4,4′-dimethoxyl-2,2′-bipyridyl under carbon mon
Some novel routes to 1-heterosubstituted 1-vinylcyclopropanes
Lewis, Richard T.,Motherwell, William B.
, p. 1465 - 1484 (2007/10/02)
3-Phenylselenoalk-1-enylidene carbenes, generated in situ by base induced condensation of α-phenylseleno carbonyl compounds and diethyl diazomethylphosphonate, can be efficiently trapped by alkenes to give alkylidene-cyclopropane adducts which undergo either [1,3] allyl selenide rearrangement or oxidative selenoxide [2,3] sigmatropic rearrangement to produce 1-phenylseleno- or 1-hydroxy-1-vinylcyclopropanes respectively.
A Novel Synthesis of Methylenecyclopropane Spiro-Linked with Cycloalkanes via a Cyclization of Allylic Epoxides and Its Application to a Synthesis of Fused 3-Methylfurans
Satoh, Tsuyoshi,Kawase, Yasushi,Yamakawa, Koji
, p. 1129 - 1135 (2007/10/02)
Ring closure of allylic epoxides derived from 1-chloroalkyl phenyl sulfoxides and cyclic ketones with lithium diisopropylamide (LDA) in 3-Exo-Tet mode gave spiro-linked methylenecyclopropanes having a hydroxyl group in good yields.Oxidation of these compounds gave ketones, which were then treated with p-toluenesulfonic acid in 1,4-dioxane or DMSO at 100 deg C to give fused 3-methylfurans in good overall yields.This procedure was applied to a synthesis of menthofuran from 4-methylcyclohexanone.
Generation, Trapping, and Adduct Rearrangement of 3-Phenylselenoalk-1-enylidene Carbenes: a Novel Direct Route to 1-Hetero-substituted 1-Vinylcyclopropanes
Lewis, Richard T.,Motherwell, William B.
, p. 751 - 753 (2007/10/02)
3-Phenylselenoalk-1-enylidene carbenes, generated in situ by base-induced Horner-Wadsworth-Emmons condensation of α-phenylseleno carbonyl compounds and diethyl diazomethylphosphonate, may be efficiently trapped to give alkylidene-cyclopropane adducts which undergo either allyl selenide rearrangement or oxidative selenoxidesigmatropic rearrangement to produce 1-heterosubstituted 1-vinylcyclopropanes.
α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. X. An Improved Synthesis of α,β-Unsaturated Carbonyl Compounds from Carbonyl Compounds with Carbon Homologation through α,β-Epoxy Sulfoxides
Satoh, Tsuyoshi,Itoh, Masayuki,Ohara, Teruhiko,Yamakawa, Koji
, p. 1839 - 1846 (2007/10/02)
Treatment of the α,β-epoxy sulfoxides derived from ketones and chloromethyl phenyl sulfoxide or 1-chloroalkyl phenyl sulfoxides with lithium perchlorate in the presence of tributylphosphine oxide in toluene at 110 deg C for about 1-3 h gave α,β-unsaturated aldehydes or α,β-unsaturated ketones in high yields.In contrast to these results, the α,β-epoxy sulfoxides derived from aldehydes did not give the desired α,β-unsaturated ketones.In this case, a sequential treatment of the α,β-epoxy sulfoxides with benzenethiolate and m-chloroperbenzoic acid afforded α-phenylsulfinylated ketones, which were heated in toluene at 110 deg C to give the desired enones in good overall yields.The oxidation of the α,β-unsaturated aldehydes obtained by this method gave α,β-unsaturated carboxylic acids in high yields.These procedures afforded a new method for the synthesis of α,β-unsaturated carbonyl compounds, including α,β-unsaturated esters, from carbonyl compounds with carbon homologation.
Magnesium Salt-Induced Opening of α,β-Epoxy Sulfoxides: A Synthesis of α-Chloro Ketones, α-Alkoxy Ketones, and α,β-Unsaturated Ketones from Carbonyl Compounds through α,β-Epoxy Sulfoxides
Satoh, Tsuyoshi,Sugimoto, Atsushi,Yamakawa, Koji
, p. 4632 - 4636 (2007/10/02)
Magnesium chloride in alcohols was found to be effective to promote the opening of α,β-epoxy sulfoxides, giving a variety of compounds such as α-chloro ketones, α-alkoxy ketones, or α,β-unsaturated ketones.The products of the reaction were dependent upon the combination of the substituents on the epoxy group of α,β-epoxy sulfoxides, magnesium salt, solvent, and reaction conditions.Keywords -- α,β-epoxy sulfoxide; epoxide; α-chloro ketone; α-alkoxy ketone; α,β-unsaturated ketone; magnesium chloride
Formylation and Acylation Reactions Catalysed by Trifluoromethanesulphonic Acid
Booth, Brian L.,El-Fekky, Teymour A.,Noori, Ghazi F. M.
, p. 181 - 186 (2007/10/02)
Regioselective formylation of toluene, m- and p-xylene, and mesitylene has been achieved by carbonylation in trifluoromethanesulphonic acid at CO pressures of 90-125 atm.In the case of cumene, the formylation reaction is in competition with disproportionation to form di- and tri-isopropylbenzenes, leading to a complex product mixture.Slow addition of cyclohexene or cyclopentene to a mixture of benzene and CF3SO3H under a high CO pressure affords 4-cyclohexylbenzaldehyde and 4-cyclopentylbenzaldehyde in 34percent and 33percent yieds, respectively, while 2-methylbut-1-ene gives 2,2,3-trimethylindanone (39percent) under similar conditions.When cyclohexene is mixed with the acid under carbon monoxide (120 atm) before addition of benzene the major products are cyclohexyl phenyl ketone and cyclohexenyl cyclohexyl ketones.
